Bob Baker has always been determined to make a living from his creative career. He started off his career by creating a music publication from scratch, with no prior experience. He didn’t let his lack of experience prevent him from achieving his goals. He just experimented with different ideas until he made it work.

Since that first publication he has expanded his interests well beyond a local music magazine. He has dabbled with writing, painting, and creating courses for aspiring artists. He even got into stand-up and improv comedy.

Bob has not let the starving artist mentality prevent him from making a career out of his creativity. In fact, he has thrived as an artist and creative.

In this episode, Bob talks about doing things that interest you, why you need to be persistent, and what separates successful artists from unsuccessful artists.

Here are three things you can learn from Bob:

Do Things That Interest You

Many of us have this fear of pursuing our creative careers. We are afraid that we will crash and burn, and never recover from our failures.

Bob takes a different approach to his creative interests. He doesn’t play it safe. He explores the things he thinks are fun. “I had this philosophy early on where, if something seemed liked it was fun to do, I was like, I want to take some action… I want to experience that and see what it’s like sooner rather than later. So, you know, a lot of people play it safe, or they wait til they know everything about a topic or they think everything’s perfect… before they dive into doing something. And I was just like, ‘I want to see what that’s like. That looks like fun.’ So I did that with comedy, with improv, with publishing a newspaper.”

It all started with creating his local music publication and has blossomed from there. Bob has never let his lack of experience stop him, and neither should you. “I published a local music newspaper and I had no business doing that whatsoever because I had no previous experience. Never wrote for the school paper, never really took journalism classes. You know, had just written on my own, had a passion for music. So I said I want to combine these two long standing passions, and just started publishing a local newspaper. And it was ugly. There were typos. People pointed things out. And I eventually learned just from doing and getting things out there to make it better.”

You Need to Be Persistent

There are no guarantees that you will ever make a living from your creative career. Not everyone is cut out for it. But there is something to be said for doing something you are passionate about.

That’s why Bob believes persistence is crucial if you want to make a career out of your art. You need to pursue it regardless of the outcome. “There are no guarantees. The world does not owe you a living. So even if you are persistent and keep your nose to the grindstone for years on end, there’s no guarantee that you’re going to make it, whatever make it means to you. However, I guess what I encourage is if you’re meant to do that thing, to express yourself in that way… You should do it regardless of the outcome. You should do it for the joy of it, however, at the same time, you could be strategic in doing it and learning the things that will move you to toward that greater potential of maybe supporting yourself some day. But hopefully it’s something that even if you don’t make a living at it or you don’t reach that point, that you’ll still do it for the joy.”

Bob recommends creating goals you can work your way towards so you can see the progress you’ve made. The key is to be strategic when you move towards your goal. “Making sure that your financial needs are met first just takes the pressure off to do your art more free flowingly I guess. And I kinda like that approach. But you can still be strategic in moving toward that goal if you have one of sustaining yourself like I did. It’s just… it may not happen on your time table… and that’s where the persistence comes in I guess. Yeah, if the payoff is not there in a month or two, are you willing to stick with it? And that’s another thing… that not everyone will, which is why not everyone succeeds because all of these rare… traits have to come together to make for a successful life.”

Being Successful vs. Being Unsuccessful

There are always people who will find success and those who won’t. There’s a fine line between success and failure.

Bob believes one of the things that separates success from failure is seeing thing through to completion. “There are tons of people that want to write a book. There’s tons of people that have started writing books. There’s tons of people who have even finished the first draft of a manuscript of a book. But there’s a very small percentage who actually follow it through to get the darn thing published. So there’s this seeing it concept, and I don’t know what quality that is, but it’s like, when you start on a project, make a commitment to chip away at it and to see it through to completion.”

Bob also sees another trait from many creative people: the need to jump from one project to the next. But you can’t always chase the shiny new object. You need discipline. “Another thing creative people are excited about new fresh things, and that’s cool, but you also have to follow through on the things that you’ve already started that may not be as exciting as they were those early weeks that you’re working on them. And that’s just a discipline I suppose and a personal commitment to stuff.”

Another thing Bob recommends is re-framing the way you look at marketing. Artists need to stop looking at marketing as a necessary evil and approach it as something that is creative. “To me the marketing thing, the necessary evil, is all about an attitude toward it. If you re-frame and realize that all you’re doing is just sharing your work with people who are going to resonate with it, that’s not painful, you know. You just gotta do it in a more strategic way. So get on friendly terms with marketing and don’t lump a lot of things into this “business” category.”

• about Bob
  • author, musician, painter, etc.
  • traces creative interests to childhood
  • wrote on his own outside of school/homework
  • also learned guitar and joined bands
  • expanded into theater, stand-up, and improv
  • published local music newspaper without any experience
  • has made a living from publishing books on music, publishing, and the arts

7:25 “I had this philosophy early on where, if something seemed liked it was fun to do, I was like, I want to take some action… I want to experience that and see what it’s like sooner rather than later. So, you know, a lot of people play it safe, or they wait til they know everything about a topic or they think everything’s perfect… before they dive into doing something. And I was just like, ‘I want to see what that’s like. That looks like fun.’ So I did that with comedy, with improv, with publishing a newspaper.”

8:04 “I published a local music newspaper and I had no business doing that whatsoever because I had no previous experience. Never wrote for the school paper, never really took journalism classes. You know, had just written on my own, had a passion for music. So I said I want to combine these two long standing passions, and just started publishing a local newspaper. And it was ugly. There were typos. People pointed things out. And I eventually learned just from doing and getting things out there to make it better.”

• how his different creative endeavors influenced each other
  • was spreading himself thin, wasn’t focusing on any one thing to support himself
  • had to make a decision to focus on something
    • decided to focus on books/writing

11:12 “Everything you do in life… is not wasted. You know, you can use those skills. Because when it came time to podcasting, or Youtube, or whatever came along, I had performance experience.”

12:07 “All this stuff feeds what you do. So I don’t feel like any of it was wasted… If anybody should ever feel like, ‘I never should have had that day job. I never should have gone down this path.’ Well, don’t beat yourself up about it because I’m sure there’s something you learned that you can implement into whatever you’re doing now.”

• choosing what path to choose
  • Bob was stubbornly determined to make a living with his creative career
  • intersection of passion/something you are attracted to and a need/want in the world
  • your work has to benefit other people
  • four reasons people create – hobby mode vs. career mode

12:48 “I encourage people to express themselves creatively first and foremost and then decide how that fits into their lives. And it’s not necessarily ‘Everyone isn’t cut out  or I have to make a living doing it or you even have to make a lot of money doing it. Sometimes it’s just personal expression and doing good in the world is enough. ”

13:13 “You don’t have to be making a living or making money or having a best seller to be worthy of pursuing a creative career.”

15:35 “If you want to make a career out of it, I think you really do need to tap into how does this benefit other people and in such a way that… at least a percentage of them are willing to pay for it… So that’s the trick that each artist or creative person needs to decide. How is what I do going to benefit people and how can I package it and present it in a way that makes people aware of what it is, they benefit from it, and they say, ‘Hell yeah I’ll buy that.’ Whether it’s a book or an album or a concert or event. It comes in many forms. But I guess that’s the best way of how to explain that choice. Sometimes you got to play with a couple different angles of it before you find one that gains traction and can actually bring in money and support it.”

• motivation for the music publication
  • New Year’s 1987 – created local publication for musicians
    • could offset cost through promotions
    • coverage of local musicians
  • learned writing, editing, graphic design, appealing to audience

19:06 “There were two audiences that I had to sell. One was the readership. I had to create content . It was an early lesson in appealing to fan base. I had to create content that would be of interest to local musicians and people involved in the local music scene. And I also had to sell it literally to advertisers that this is getting read. So if I had the readership… covered, then I thought it would be more likely that local music stores and recording studios would pay to run display ads to reach my audience.”

• contacting people for publication
  • started by writing everything himself
  • once it was out, writers contacted him
  • potential advertisers would also act as distributions (music stores)
  • saw first hand someone engaging with content at a music store
  • not waiting for experience for doing something
  • focusing locally
  • also built his authorship audience slowly
  • The Empowered Artist book Bob wrote

23:16 “I think that’s really smart, especially when you’re early in your career, early in a new project, to really hyper focus… So yeah, I focused on places where musicians went. And as it gained traction,  I expanded to my hang outs like coffee shops and restaurants. Like cool hangouts… because I know the readership didn’t filter over into fans of bands I covered… I focused on the musician then expanded.”

24:44 “It helps to start in one niche and then slowly widen the gap than to start broad right out of the gate. It’s a little tougher to get traction that way.”

• 1,000 True Fans by Kevin Kelly
  • making a living from 1,000 people who are extremely dedicated to your work
  • don’t get obsessed with the numbers, but be aware of the general concept
  • a core group of fans can support an artist – cites himself as an example
  • having much smaller following than celebrities, but still being able to live off your work
  • there are many people making a living off their art that you don’t know about
  • Michael Laskow’s company: Taxi
    • Musical Middle Class/Creative Middle Class – people between chart toppers and starving artists
    • serve their audiences and make a living from their art
  • reaching many people through the internet but also being a hard place to reach people
  • why not me vs. why me
    • new crops of people are always making it through
• power of persistence
  • what’s your motivation or why?
  • Big Magic by Elizabeth Gilbert
    • having a day job to support your creativity

31:04 “One thing I kinda gotten a little wiser about, again not everyone is cut out to be self-employed. Not everyone has… the tolerance to learn all the wide array of things you need to learn and embrace all the tools… I’ve written and taught a lot over the years about marketing, and there are tons of people out there that just curse marketing, and they hate it, and they think it’s a necessary evil… You’re not going to really do well promoting yourself or sharing what you have if you think of marketing in that way.”

32:09 “There are no guarantees. The world does not owe you a living. So even if you are persistent and keep your nose to the grindstone for years on end, there’s no guarantee that you’re going to make it, whatever make it means to you. However, I guess what I encourage is if you’re meant to do that thing, to express yourself in that way… You should do it regardless of the outcome. You should do it for the joy of it, however, at the same time, you could be strategic in doing it and learning the things that will move you to toward that greater potential of maybe supporting yourself some day. But hopefully it’s something that even if you don’t make a living at it or you don’t reach that point, that you’ll still do it for the joy.”

33:45 “Making sure that your financial needs are met first just takes the pressure off to do your art more free flowingly I guess. And I kinda like that approach. But you can still be strategic in moving toward that goal if you have one of sustaining yourself like I did. It’s just… it may not happen on your time table… and that’s where the persistence comes in I guess. Yeah, if the payoff is not there in a month or two, are you willing to stick with it? And that’s another thing… that not everyone will, which is why not everyone succeeds because all of these rare… traits have to come together to make for a successful life.”

• what separates people who “make it” vs. those who don’t
  • the ability to focus and see things through
  • has interviewed people over the years who have done well in their fields
  • he notices patterns and what works, and compares it to his own success stories
  • is both creative and analytical
  • relieving tension by finishing things instead of getting distracted by new things

36:29 “There are tons of people that want to write a book. There’s tons of people that have started writing  books. There’s tons of people who have even finished the first draft of a manuscript of a book. But there’s a very small percentage who actually follow it through to get the darn thing published. So there’s this seeing it concept, and I don’t know what quality that is, but it’s like, when you start on a project, make a commitment to chip away at it and to see it through to completion.”

37:14 “Another thing creative people are excited about new fresh things, and that’s cool, but you also have to follow through on the things that you’ve already started that may not be as exciting as they were those early weeks that you’re working on them. And that’s just a discipline I suppose and a personal commitment to stuff.”

37:49 “To me the marketing thing, the necessary evil, is all about an attitude toward it. If you re-frame and realize that all you’re doing is just sharing your work with people who are going to resonate with it, that’s not painful, you know.  You just gotta do it in a more strategic way. So get on friendly terms with marketing and don’t lump a lot of things into this “business” category.”

38:27 “But marketing, I don’t think of it as being part of the business aspect, the heavy, dreary business. I think of it as being fun and creative and spontaneous as art. It can be just as creative, I should say, as whatever the work is that you do.”

• creative things he’s done with marketing
  • got on the internet on 1995
    • main form of communicating was the written word: email, articles, etc.
  • viewed new tech as a way to reach new audiences
    • “How can I provide value?”
  • Facebook Live  |  Youtube Live  |  Periscope
    • scheduling AMAs
  • Empowered Artist Mastermind
  • Facebook Live videos are saved for later consumption
  • video tours, painting demonstrations, live gigs/performances/taking requests, etc.
  • getting noticed when you jump on new tech early
  • be playful with your art/career
  • “What if I…”
  • improv – everyone should take an improv class even if you are scared
    • makes you comfortable with uncertainty
    • Yes and…
      • accepting what your partner gives you and adding something to the scene
    • teamwork in improv
      • active listening and making your partner look good
    • encouraging sillyness and being childlike

44:30 “I think that’s a great point and a great attitude to embrace in regardless is that we are all making this up as we go along. A lot of people when they say “Oh I’m going to get serious about my art, and I’m going to making it a career.’ So they read all the books and they want to know exactly the right path to take. So my take on that is, yeah educate yourself. Learn about it… but there is no one right path.”

46:05 “I recommend anyone take an improv class, especially if it scares you. That’s perfect. It really forces you to be open minded and to trust yourself and to be comfortable with uncertainty.”

46:46 “Wouldn’t it be a greater way to approach a career in the arts? It’s like this whole series of things you’re experimenting with and playing with and you notice some of the ones that resonate and some of the ones you enjoy more and do more of those. And you do less of those that didn’t quite pan out? And always be looking at the new thing you can play with. But you may just find something that really works and connects that you can focus on.”

• Bob’s book in School of Rock
• teaching music marketing course at Berklee College of Music
  • teaching students all over the world
  • honed his teaching skills

54:05 “When you put yourself out there and you sort of stake your claim on whatever your identity is and you just show commitment and quality over the years, opportunities will come to you.”

• advice for people who are stuck trying to figure out how to sell their work
  • visual artists who are trying to get into galleries
    • stop knocking on doors that won’t open
  • ask yourself open ended questions
  • stop asking unempowered questions, ask more empowering questions
    • What can I do that will blow people away?
    • What can I do that is different and will get attention?
    • start brainstorming answers and pick one
  • if you are doing something solo, try group events
  • How can you collaborate with others and have a collective group attract art fans?
  • Bob’s course on creating compelling writing to get people to buy.
    • describe what you do to pull people in and make what you offer more compelling
  • shake things up and ask for the sale
  • Amanda Palmer – TED Talk and book on asking

1:02:10 “Make people aware that you have stuff for sale and don’t be afraid to ask for a sale and determine a price, and when somebody asks you, state it as confidentially as you can, which is really tough. I know, even I struggle with this stuff. Just state it and shut up and wait for their response.”

• favorite quote
  • documentary on The Roosevelts
  • “Do what you can, with what you have, where you are.” ― Theodore Roosevelt
  • the importance of taking action
  • How can I experience this sooner?
  • people always come up with excuses
  • examine the excuses you are giving
  • there is no right time
• morning routine
  • get up by 7am
  • warm glass of water with lemon squeeze and apple cider vinegar
  • does morning pages style journaling
  • listen/read something inspirational/spiritual/positive
  • meditates for 20 minutes
  • get some movement going with dancing/stretches
  • eat breakfast/smoothie/coffee
  • does creative stuff in the early hours
• books, podcasts, documentaries
  • Big Magic by Elizabeth Gilbert and TED Talks on creativity
    • Magic Lessons podcast
  • Empowered Artist by Bob Baker
• creative people
  • Laura Hall and Colin Mochrie from Whose Line Is It Anyway?
  • Jack Conte of Pomplamoose and founder of Patreon
  • Richard Branson of Virgin empire
• definition of creativity

1:13:09 “Creativity to me is basically the human instinct or drive for self-expression and I guess that’s one of the things that separates us from other species on the planet… We have these individual drives or talents or instincts to do certain things, and I think it’s just part of our being human to express ourselves. And I think a lot of the frustration in the world is people who don’t give themselves permission to fully express who they are.”

• being more creative

1:14:08 “Prioritize your art to realize that that self-expression is important and to actually put it on your calendar… treat it with the respect that it deserves because for most people creativity is something… only people do when they get around to it, after everything else is done, so move that up on your priority list and actually block out times on the calendar every week… and honor those commitments to yourself. Again, just don’t do when you get around to it, because that’s a mystery fantasy land that never comes.”

• challenge
  • pick a little project you’ve been putting off, and choose a doable thing in an hour or less
  • write it down and do it
  • celebrate completing it

Bob Baker‘s hub for all his work  |  Twitter